Potassium Carbonate → 1-(3,4,5-Trimethoxy-benzoyl)-3-[2-[4-(hydroxy-diphenyl-methyl)-piperidin-1-yl]-ethyl]-3-(3,4-dimethoxy-phenyl)-pyrrolidine

HRID 2269848Notes

Reaction equation

HRID 2269848 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:29]=[C:30]([O:34][CH3:35])[C:31]=1[O:32][CH3:33])[C:6]([N:8]1[CH2:12][CH2:11][C:10]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[CH:20]=2)([CH2:13][CH2:14]S(C)(=O)=O)[CH2:9]1)=[O:7].[OH:36][C:37]([C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[CH:38]1[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C.CO>CN(C)C=O.ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:29]=[C:30]([O:34][CH3:35])[C:31]=1[O:32][CH3:33])[C:6]([N:8]1[CH2:12][CH2:11][C:10]([CH2:13][CH2:14][N:41]2[CH2:42][CH2:43][CH:38]([C:37]([OH:36])([C:44]3[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=3)[C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)[CH2:39][CH2:40]2)([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[CH:20]=2)[CH2:9]1)=[O:7]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 15723AzacyclonolHCID 155428821-(3,4,5-Trimethoxy-benzoyl)-3-(3,4-dimethoxy-phenyl)-3-(2-methanesulfonyl-ethyl)-pyrrolidineHCID 21584119Ethylacetate methanol

Product 1

HCID 102337191-(3,4,5-Trimethoxy-benzoyl)-3-[2-[4-(hydroxy-diphenyl-methyl)-piperidin-1-yl]-ethyl]-3-(3,4-dimethoxy-phenyl)-pyrrolidine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

Combine 1-(3,4,5-trimethoxy-benzoyl)-3-(3,4-dimethoxy-phenyl)-3-(2-methanesulfonyl-ethyl)-pyrrolidine (0.50 g, 0.96 mmol), 4-(hydroxy-diphenyl-methyl)-piperidine (0.39 g, 1.44 mmol), and potassium carbonate (0.60 g, 4.34 mmol) in dimethylformamide (30 mL). Heat to 80° C. After 48 hours, cool and evaporate in vacuo to obtain a residue. Partition the residue between ethyl acetate and water. Extract the organic layer with water and a saturated solution of potassium carbonate. Dry the organic layer over Na2SO4, filter, and concentrate in vacuo to obtain a residue. Chromatograph the residue on silica gel eluting with 5/1 ethyl acetate/methanol to give a foam. Combine the foam with dichloromethane and extract with 5% sodium bicarbonate solution. Dry the organic layer over Na2SO4, filter, and concentrate in vacuo at 65° C. to obtain the title compound: Rf=0.21 (silica gel, 5/1 ethyl acetate/methanol); mp; 95-97° C.

Workup

  1. temperaturecool
  2. customevaporate in vacuo
  3. customto obtain a residue
  4. customPartition the residue between ethyl acetate and water
  5. extractionExtract the organic layer with water
  6. dry with materialDry the organic layer over Na2SO4
  7. filtrationfilter
  8. concentrationconcentrate in vacuo
  9. customto obtain a residue
  10. extractionextract with 5% sodium bicarbonate solution
  11. dry with materialDry the organic layer over Na2SO4
  12. filtrationfilter
  13. concentrationconcentrate in vacuo at 65° C.

Sources & evidence

ORD record
ord-65be1231287a4e9182ad33dbf5da9362
Source dataset
uspto-grants-2001_12
Patent number
US06329392B1

Reaction notes

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